Caffeic Acid: a Review of Its Potential Use in Medications and Cosmetics
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Enzymatic Synthesis of 1-Sinapoylglucose from Free
Enzymatic Synthesis of 1-Sinapoylglucose from Free Sinapic Acid and UDP-Glucose by a Cell-Free System from Raphanus sativus Seedlings Dieter Strack Botanisches Institut der Universität zu Köln, Gyrhofstr. 15, D-5000 Köln 41 Z. Naturforsch. 35 c, 204-208 (1980); received December 28, 1979 Raphanus, Brassicaceae, Phenylpropanoid Metabolism, Glucose Ester, Esterification. Protein extracts from seedlings of Raphanus sativus catalyze the transfer of the glucosyl moiety of UDP-glucose to the carboxyl group of phenolic acids. Enzymatic activity was determined spec- trophotometrically by measuring the increase in absorbance at 360 nm and/or by the aid of high performance liquid chromatography (HPLC). From 12 phenolic acids tested as acceptors, sinapic acid was by far the best substrate. The glu- cosyltransfer to sinapic acid has a pH optimum near 7 and requires as SH group for activity, p- Chloromercuribenzoate (PCMB) inhibits activity, which can be restored by the addition of di- thiothreitol (DTT). The formation of 1-sinapoylglucose was found to be a reversible reaction, sin ce the addition of UDP results in a breakdown of the ester. Introduction Materials and Methods Higher plants contain a large number of various Plant material and culture conditions are described hydroxycinnamoyl esters. Most of them might be elsewhere [10]. synthesized via hydroxycinnamoyl-CoA thiolesters as the activated reaction partners [1]. The widely Thin-layer chromatography occurring glucose esters [2], however, might be Phenolic acid derivatives were chromatographed exclusively synthesized from free hydroxycinnamic on microcrystalline cellulose (Avicel) in CAW, chlo acids and UDP-glucose [3, 4]. The formation of roform - acetic acid - water (3 : 2, water saturated) glucose esters of benzoic acids might follow the same and were detected under UV with and without NH3- mechanism [5], vapor. -
Phenolic Compounds in Coffee1
M I N I R E V I E W Phenolic compounds in coffee1 Adriana Farah and Carmen Marino Donangelo* Laboratório de Bioquímica Nutricional e de Alimentos. Departamento de Bioquímica, Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, CT, Bloco A, Sala 528-A. Ilha do Fundão, Rio de Janeiro, RJ, 21949-900, Brazil. *Corresponding author: [email protected] Phenolic compounds are secondary metabolites generally involved in plant adaptation to environmental stress conditions. Chlorogenic acids (CGA) and related compounds are the main components of the phenolic fraction of green coffee beans, reaching levels up to 14 % (dry matter basis). These compounds have a number of beneficial health properties related to their potent antioxidant activity as well as hepatoprotective, hypoglycemic and antiviral activities. The main groups of CGA found in green coffee beans include caffeoylquinic acids, dicaffeoylquinic acids, feruloylquinic acids, p-coumaroylquinic acids and mixed diesters of caffeic and ferulic acids with quinic acid, each group with at least three isomers. During coffee processing, CGA may be isomerized, hydrolyzed or degraded into low molecular weight compounds. The high temperatures of roasting also produce transformation of part of CGA into quinolactones and, along with other compounds, melanoidins. This review focuses on the chemical characteristics, biosynthesis, and distribution of CGA and related compounds in coffee. The influence of genetic, physiological and environmental factors as well as processing on the chemical composition of coffee beans is discussed. The impact of CGA composition of green coffee on cup quality is also approached. Despite the existence of substantial published information on the total levels of CGA in coffee, more research is needed on the composition of minor phenolic compounds and specific CGA isomers (and related substances) in green and roasted coffee beans, as well as their impact on coffee quality. -
Metabolomics Reveals the Molecular Mechanisms of Copper Induced
Article Cite This: Environ. Sci. Technol. 2018, 52, 7092−7100 pubs.acs.org/est Metabolomics Reveals the Molecular Mechanisms of Copper Induced Cucumber Leaf (Cucumis sativus) Senescence † ‡ § ∥ ∥ ∥ Lijuan Zhao, Yuxiong Huang, , Kelly Paglia, Arpana Vaniya, Benjamin Wancewicz, ‡ § and Arturo A. Keller*, , † Key Laboratory of Pollution Control and Resource Reuse, School of Environment, Nanjing University, Nanjing, Jiangsu 210023, China ‡ Bren School of Environmental Science & Management, University of California, Santa Barbara, California 93106-5131, United States § University of California, Center for Environmental Implications of Nanotechnology, Santa Barbara, California 93106, United States ∥ UC Davis Genome Center-Metabolomics, University of California Davis, 451 Health Sciences Drive, Davis, California 95616, United States *S Supporting Information ABSTRACT: Excess copper may disturb plant photosynthesis and induce leaf senescence. The underlying toxicity mechanism is not well understood. Here, 3-week-old cucumber plants were foliar exposed to different copper concentrations (10, 100, and 500 mg/L) for a final dose of 0.21, 2.1, and 10 mg/plant, using CuSO4 as the Cu ion source for 7 days, three times per day. Metabolomics quantified 149 primary and 79 secondary metabolites. A number of intermediates of the tricarboxylic acid (TCA) cycle were significantly down-regulated 1.4−2.4 fold, indicating a perturbed carbohy- drate metabolism. Ascorbate and aldarate metabolism and shikimate- phenylpropanoid biosynthesis (antioxidant and defense related pathways) were perturbed by excess copper. These metabolic responses occur even at the lowest copper dose considered although no phenotype changes were observed at this dose. High copper dose resulted in a 2-fold increase in phytol, a degradation product of chlorophyll. -
GRAS Notice GRN 868 Agency Response Letter -Coffee Fruit Extract
U.S. FOOD & DRUG ADMINISTRATI ON CENTER FOR FOOD SAFETY &APPLIED NUTRITION Ashish Talati Amin Talati Wasserman, LLP 100 S. Wacker Drive Suite 2000 Chicago, IL 60606 Re: GRAS Notice No. GRN 000868 Dear Mr. Talati: The Food and Drug Administration (FDA, we) completed our evaluation of GRN 000868. We received the notice that you submitted on behalf of VDF FutureCeuticals, Inc. (VDF) on June 10, 2019, and filed it on August 19, 2019. VDF submitted an amendment to the notice on November 1, 2019, that clarified information related to the description of coffee fruit extract, batch compliance with specifications, dietary exposure, safety studies, and analytical method validation. The subject of the notice is coffee fruit extract for use as an ingredient and as an antioxidant in certain beverages, including flavored waters, coffee, tea, ready-to-mix (RTM) beverages, fruit juices, and vegetable juices/blends; nutritional and replacement milk products (pre-workout); clusters/bars; chocolate; candy; and chewing gum, at levels ranging from 20 mg to 300 mg/serving.1 This notice informs us of VDF ' sview. that these uses of coffee fruit extract are GRAS through scientific procedures. Our use of the term, "coffee fruit extract" in this letter is not our recommendation of that term as an appropriate common or usual name for declaring the substance in accordance with FDA's labeling requirements. Under 21 CFR 101.4, each ingredient must be declared by its common or usual name. In addition, 21 CFR 102.5 outlines general principles to use when establishing common or usual names for nonstandardized foods. -
Protective Effect of Caffeic Acid Phenethyl Ester on Myocardial Injury Due to Anti-Oxidant Action
Editorial Comment 583 Protective effect of caffeic acid phenethyl ester on myocardial injury due to anti-oxidant action Caffeic acid phenethyl ester (CAPE) is an important active difference between present and previous studies is that CAPE component of propolis (a honey-bee hive extract). Propolis con- was given to animals over a subacute period (7 days), whereas tains >300 active constituents, with flavonoids, phenolic acids, it was given acutely in previous studies. Furthermore, we show phenolic acid esters, terpenoids, steroids and amino acids being that CAPE improves the level of NO that falls in the rat hearts among the main components (1). after ISO administration. İlhan et al. (5) infer that the slight hypo- Caffeic acid phenethyl ester was first chemically synthe- tensive effect of the agent will be balanced in this subacute sized at Columbia University in 1988 (2), and was subsequently period and CAPE can act as positive inotropic agent by inducing considered to be a potent anti-cancer component of propolis (3), beta-adrenoceptors and dilating coronary arteries, and inducing as well as being a potent anti-inflammatory and anti-oxidant NO without affecting blood pressure. This study provides a new agent. The interaction of these 2 main properties with other viewpoint that CAPE might be useful in both hypertensive and molecular actions of CAPE means that it possesses a plethora of normotensive patients with a heart attack. important biological activities. CAPE showed promising efficacy Furthermore, İlhan et al. (5) proved that AST and LDH levels in both in vitro and in vivo studies of animal models, with mini- in L-NNA+ISO group are significantly increased compared to mum adverse effects, its effectiveness being demonstrated in control group. -
Research 1..8
See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/221902546 Influence of Fungal Endophyte Infection on Phenolic Content and Antioxidant Activity in Grasses: Interaction between Lolium perenne and Different Strains of Neotyphodium lolii Article in Journal of Agricultural and Food Chemistry · March 2012 DOI: 10.1021/jf204105k · Source: PubMed CITATIONS READS 34 339 4 authors, including: Abdel Qawasmeh Hassan K Obied Hebron University Charles Sturt University 7 PUBLICATIONS 149 CITATIONS 38 PUBLICATIONS 1,177 CITATIONS SEE PROFILE SEE PROFILE Warwick Wheatley Charles Sturt University 10 PUBLICATIONS 99 CITATIONS SEE PROFILE Some of the authors of this publication are also working on these related projects: Ethnobotany: A living Science for Alleviating Human Suffering View project Pharmacist perception and knowledge about CAM. View project All content following this page was uploaded by Abdel Qawasmeh on 01 January 2019. The user has requested enhancement of the downloaded file. Article pubs.acs.org/JAFC Influence of Fungal Endophyte Infection on Phenolic Content and Antioxidant Activity in Grasses: Interaction between Lolium perenne and Different Strains of Neotyphodium lolii Abdelqader Qawasmeh,† Hassan K. Obied,*,§ Anantanarayanan Raman,† and Warwick Wheatley† † School of Agricultural and Wine Sciences, Charles Sturt University, Orange, NSW 2800, Australia § School of Biomedical Sciences, Charles Sturt University, Wagga Wagga, NSW 2678, Australia ABSTRACT: Lolium perenne is a major forage and turf grass, which is often naturally infected with a “wild-type” strain (EWT)of the fungal endophyte Neotyphodium lolii, establishing a symbiotic relationship. In this study, the impacts of different strains wild type EWT, AR1 (EAR1) and AR37 (EAR37), of N. -
Down Regulation of P-Coumarate 3-Hydroxylase in Petunia Uniquely
www.nature.com/scientificreports OPEN Down regulation of p-coumarate 3-hydroxylase in petunia uniquely alters the profle of emitted foral Received: 18 January 2019 Accepted: 25 April 2019 volatiles Published: xx xx xxxx Joo Young Kim, Robert T. Swanson, Maria I. Alvarez, Timothy S. Johnson, Keun H. Cho , David G. Clark & Thomas A. Colquhoun Petunia × hybrida cv ‘Mitchell Diploid’ foral volatile benzenoid/phenylpropanoid (FVBP) biosynthesis ultimately produces foral volatiles derived sequentially from phenylalanine, cinnamic acid, and p- coumaric acid. In an attempt to better understand biochemical steps after p-coumaric acid production, we cloned and characterized three petunia transcripts with high similarity to p-coumarate 3-hydroxylase (C3H), hydroxycinnamoyl-CoA:shikimate/quinate hydroxycinnamoyl transferase (HCT), and cafeoyl shikimate esterase (CSE). Transcript accumulation of PhC3H and PhHCT was highest in fower limb tissue during open fower stages. PhCSE transcript accumulation was also highest in fower limb tissue, but it was detected earlier at initial fower opening with a bell-shaped distribution pattern. Down regulation of endogenous PhC3H transcript resulted in altered transcript accumulation of many other FVBP network transcripts, a reduction in foral volatiles, and the emission of a novel foral volatile. Down regulation of PhHCT transcript did not have as large of an efect on foral volatiles as was observed for PhC3H down regulation, but eugenol and isoeugenol emissions were signifcantly reduced on the downstream foral volatiles. Together these results indicate that PhC3H is involved in FVBP biosynthesis and the reduction of PhC3H transcript infuences FVBP metabolism at the network level. Additional research is required to illustrate PhHCT and PhCSE functions of petunia. -
Flavonols, Phenolic Acids and Antioxidant Activity of Some Red
Stark,A., A. Nyska,A. Zuckerman, and Z. MadarChanges in intestinal Vincken,J,-P., H. A. Schols, R. J. F. J. )omen,K. Beldnan, R. G. F. Visser, Tunicamuscularis following dietary liber feeding inrats. A morphometric andA. G. J. Voragen'.Pectin - the hairy thing. ln. Voragen, E,H. Schools, studyusing image analysis. Dig Dis Sci 40, 960-966 (1995). andB. t4sser(Eds.): Advances inPectin and Pectinase Research, 4Z-5g. Stark,A., A. Nyska, and Z. Madar. I\4etabolic and morphometric changes KlumerAcademic Publishers, Dortrecht, Niederlande (2003). insmall and large intestine inrats fed high-fiber diets. Toxicol pathol 24, Yoo,S.-H., M. Marshall, A.Hotchkiss, and H. G. Lee: Viscosimetric beha- 166-171(1996). vioursof high-methoxy andlow-methoxy pectin solutions. Food Hydro- Sugawa-Katayama,Y.,and A. ltuza.Morphological changes of smallin- coll20, 62-67 (2005). testinalmucosa inthe rats fed high pectin diets. Oyo Toshitsu Kagaku 3, Zhang,J., and J. fr. Lupton: Dielary fibers stimulate colonic cell prolifera- 335-341(1994) (in Japanisch). tionby different mechanisms atdifferent sites. Nutr Cancer ZZ.26l-276 Tamura,M., and H. SuzukiEffects of pectinon jejunaland ileal mor- (1 994) phologyand ultrastructurein adultmice. Ann Nutr Metab 41, 2SS-259 (1997) Flavonols,Phenolic Acids and Antioxidant Activity of Some Red Fruits LidijaJakobek#, Marijan Seruga, lvana Novak and MailinaMedvidovi6-Kosanovi6 DepartmentofApplied Chemistry and Ecology, Faculty of Food Technology,J J StrossmayerUniversity of0sijek, Kuhaceva 18, HR-31000 0sijek, Croatia Summary schwarzeund rote Johannisbeere) wurde mittelsHPlC-Methode be- Redfruits (blueberry, blackberry, chokeberry, strawberry, red raspberry, stimmt.Die Verbindungen wurden als Aglykon nach der Hydrolyse mit sweetcherry, sour cherry, elderberry, black currant and red currant) were 1,2mol dm 3 HCI analysiert. -
Electrochemical Tools for Determination of Phenolic Compounds in Plants
Int. J. Electrochem. Sci., 8 (2013) 4520 - 4542 International Journal of ELECTROCHEMICAL SCIENCE www.electrochemsci.org Electrochemical Tools for Determination of Phenolic Compounds in Plants. A Review Jiri Dobes1, Ondrej Zitka1,2,3,4, Jiri Sochor1,5, Branislav Ruttkay-Nedecky1,3, Petr Babula1,3, Miroslava Beklova3,4, Jindrich Kynicky3,5,6, Jaromir Hubalek2,3, Borivoj Klejdus1, Rene Kizek1,2,3, Vojtech Adam1,2,3* 1Department of Chemistry and Biochemistry, Faculty of Agronomy, Mendel University in Brno, Zemedelska 1, CZ-613 00 Brno, Czech Republic, European Union 2Department of Microelectronics, Faculty of Electrical Engineering and Communication, Brno University of Technology, Technicka 10, CZ-616 00 Brno, Czech Republic, European Union 3Central European Institute of Technology, Brno University of Technology, Technicka 3058/10, CZ- 616 00 Brno, Czech Republic, European Union 4Department of Veterinary Ecology and Environmental Protection, Faculty of Veterinary Hygiene and Ecology, University of Veterinary and Pharmaceutical Sciences, Palackeho 1-3, CZ-612 42 Brno, Czech Republic, European Union 5Vysoka skola Karla Englise, Sujanovo nam. 356/1, CZ-602 00 Brno, Czech Republic, European Union 6Department of Geology and Pedology, Faculty of Forestry and Wood Technology, Mendel University in Brno, Zemedelska 1, CZ-613 00 Brno, Czech Republic, European Union *E-mail: [email protected] Received: 2 January 2013 / Accepted: 3 February 2013 / Published: 1 April 2013 Electrochemical methods are a reliable tool for a fast and low cost assay of phenolic compounds (phenolics) in food samples. The methods are precise and sesnitive enough to assay low content of polyphenols. The devices can be stationary or flow through, and based on voltammetry or amperometry. -
Verbascoside — a Review of Its Occurrence, (Bio)Synthesis and Pharmacological Significance
Biotechnology Advances 32 (2014) 1065–1076 Contents lists available at ScienceDirect Biotechnology Advances journal homepage: www.elsevier.com/locate/biotechadv Research review paper Verbascoside — A review of its occurrence, (bio)synthesis and pharmacological significance Kalina Alipieva a,⁎, Liudmila Korkina b, Ilkay Erdogan Orhan c, Milen I. Georgiev d a Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria b Molecular Pathology Laboratory, Russian Research Medical University, Ostrovityanova St. 1A, Moscow 117449, Russia c Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey d Laboratory of Applied Biotechnologies, Institute of Microbiology, Bulgarian Academy of Sciences, Plovdiv, Bulgaria article info abstract Available online 15 July 2014 Phenylethanoid glycosides are naturally occurring water-soluble compounds with remarkable biological proper- ties that are widely distributed in the plant kingdom. Verbascoside is a phenylethanoid glycoside that was first Keywords: isolated from mullein but is also found in several other plant species. It has also been produced by in vitro Acteoside plant culture systems, including genetically transformed roots (so-called ‘hairy roots’). Verbascoside is hydro- fl Anti-in ammatory philic in nature and possesses pharmacologically beneficial activities for human health, including antioxidant, (Bio)synthesis anti-inflammatory and antineoplastic properties in addition to numerous wound-healing and neuroprotective Cancer prevention Cell suspension culture properties. Recent advances with regard to the distribution, (bio)synthesis and bioproduction of verbascoside Hairy roots are summarised in this review. We also discuss its prominent pharmacological properties and outline future Phenylethanoid glycosides perspectives for its potential application. Verbascum spp. © 2014 Elsevier Inc. All rights reserved. Contents Treasurefromthegarden:thediscoveryofverbascoside,anditsoccurrenceanddistribution.......................... -
Anti-Inflammatory, Antipyretic, and Analgesic Properties Of
molecules Article Anti-Inflammatory, Antipyretic, and Analgesic Properties of Potamogeton perfoliatus Extract: In Vitro and In Vivo Study Samar Rezq 1 , Mona F. Mahmoud 1,* , Assem M. El-Shazly 2 , Mohamed A. El Raey 3 and Mansour Sobeh 4,* 1 Department of Pharmacology and Toxicology, Faculty of Pharmacy, Zagazig University, Zagazig 44519, Egypt; [email protected] 2 Department of Pharmacognosy, Faculty of Pharmacy, Zagazig University, Zagazig 44519, Egypt; [email protected] 3 National Research Centre, Department of Phytochemistry and Plant Systematics, Pharmaceutical Division, Dokki, Cairo 12622, Egypt; [email protected] 4 AgroBioSciences Research, Mohammed VI Polytechnic University, Lot 660–Hay MoulayRachid, Ben-Guerir 43150, Morocco * Correspondence: [email protected] (M.F.M.); [email protected] (M.S.) Abstract: Natural antioxidants, especially those of plant origins, have shown a plethora of biological activities with substantial economic value, as they can be extracted from agro-wastes and/or under exploited plant species. The perennial hydrophyte, Potamogeton perfoliatus, has been used traditionally to treat several health disorders; however, little is known about its biological and its medicinal effects. Here, we used an integrated in vitro and in vivo framework to examine the potential effect of P. perfoliatus on oxidative stress, nociception, inflammatory models, and brewer’s yeast-induced pyrexia in mice. Our results suggested a consistent in vitro inhibition of three enzymes, namely 5-lipoxygenase, cyclooxygenases 1 and 2 (COX-1 and COX-2), as well as a potent antioxidant effect. Citation: Rezq, S.; Mahmoud, M.F.; These results were confirmed in vivo where the studied extract attenuated carrageenan-induced paw El-Shazly, A.M.; El Raey, M.A.; Sobeh, edema, carrageenan-induced leukocyte migration into the peritoneal cavity by 25, 44 and 64% at 200, M. -
Coa LIGASE, FERULOYL-Coa REDUCTASE and CONIFERYL ALCOHOL OXIDOREDUCTASE
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Elsevier - Publisher Connector Volume 31, number 3 FEBS LETTERS May 1973 THREE NOVEL ENZYMES INVOLVED IN THE REDUCTION OF FERULIC ACID TO CONIFERYL ALCOHOL IN HIGHER PLANTS: FERULATE: CoA LIGASE, FERULOYL-CoA REDUCTASE AND CONIFERYL ALCOHOL OXIDOREDUCTASE G.G. GROSS, J’. STGCKIGT, R.L. MANSELL* and M.H. ZENK Lehrstuhl fiir Pjlanzenphysiologie, Ruhr-Universitbt, 463 Bochum, Germany Received 1 March 1973 1. Introduction cambial tissue, of phytotron grown Forsythia sp. were used. The tissue was frozen in liquid nitrogen Using a cell-free system from cambial tissue of and powdered. To the powder was added polyclar AT Sulix alba the reduction of ferulate to coniferyl alco- (w/w) and the mixture subsequently extracted with hol has been shown for the first time, unequivocally, 0.1 M borate buffer pH 7.8 supplemented with lop2 to occur in higher plants [l] . This conversion is de- M 2-mercaptoethanol. After centrifugation the super- pendent on ATP, CoA and reduced pyridine nucleo- natant was fractionated with ammonium sulfate and tides. A reaction sequence has been postulated on the the fraction between 35 and 72% was resuspended in basis of these experiments involving the intermediate the same buffer as above. This solution was treated formation of feruloyl-CoA and coniferyl aldehyde with an anion exchanger and used as a crude enzyme which is in accordance with previous assumptions for source. For the detection of the feruloyl-CoA reduc- this mechanism in lignin biosynthesis as recently re- tase, the above enzyme solution was further fraction- viewed [2].